Hydrochloric Acid → (3S)-piperidine-3-carboxylic acid hydrochloride

HRID 1771935Notes

Reaction equation

HRID 1771935 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([C:14]([OH:16])=[O:15])[CH2:9]1)=O)(C)(C)C.[ClH:17]>C(O)(=O)C>[ClH:17].[NH:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([C:14]([OH:16])=[O:15])[CH2:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 6951168(3S)-1-((tert-butoxy)carbonyl)piperidine-3-carboxylic acid

Product 1

HCID 24820453(3S)-piperidine-3-carboxylic acid hydrochlorideYield 99.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
15 °C

Procedure

(S)-Piperidine-1,3-dicarboxylic acid 1-tert-butyl ester (20 kg, 87.2 mol) was slurried in acetic acid (189 kg) and cooled to 15° C. An excess of hydrogen chloride gas (9.6 kg) was charged and stirred for ˜4 hours to complete deprotection. The slurry was isolated and filter-cake rinsed with acetic acid (2×31.5 kg). The filter cake was then vacuum dried to obtain product (14.4 kg).

Workup

  1. customThe slurry was isolated
  2. filtrationfilter-cake
  3. washrinsed with acetic acid (2×31.5 kg)
  4. customvacuum dried

Sources & evidence

ORD record
ord-925b7b092fbe451aa4d191be1ffa875b
Source dataset
uspto-grants-2016_02
Patent number
US09249155B2

Reaction notes

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